uridine monophosphate

同

UMP

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/09/23 00:09:41」(JST)

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Uridine monophosphate

Names
IUPAC name [(2R,3S,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names Uridylic acid; Uridine 5'-monophosphate; 5'-Uridylic acid; Uridine 5'-phosphate; Uridine phosphate; 5'-UMP; Uridine 5'-phosphoric acid
Identifiers
CAS Number	58-97-9 Y
3D model (JSmol)	Interactive image
ChemSpider	5808 N
ECHA InfoCard	100.000.371
IUPHAR/BPS	5125
MeSH	Uridine+monophosphate
PubChem CID	6030
InChI InChI=1S/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 N Key: DJJCXFVJDGTHFX-XVFCMESISA-N N InChI=1/C9H13N2O9P/c12-5-1-2-11(9(15)10-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H,10,12,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 Key: DJJCXFVJDGTHFX-XVFCMESIBD
SMILES c1cn(c(=O)[nH]c1=O)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
Properties
Chemical formula	C9H13N2O9P
Molar mass	324.18 g·mol−1
Melting point	202 °C (396 °F; 475 K) (decomposes)
Solubility in water	good, also in methanol
Acidity (pKa)	1.0, 6.4, 9.5
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Uridine monophosphate (UMP), also known as 5′-uridylic acid (conjugate base uridylate), is a nucleotide that is used as a monomer in RNA. It is an ester of phosphoric acid with the nucleoside uridine. UMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase uracil; hence, it is a ribonucleotide monophosphate. As a substituent or radical its name takes the form of the prefix uridylyl-. The deoxy form is abbreviated dUMP. Covalent attachment of UMP (e.g. to a protein such as adenylyltransferase) is called uridylylation (or sometimes uridylation).

Biosynthesis

Uridine monophosphate is formed from Orotidine 5'-monophosphate (orotidylic acid) in a decarboxylation reaction catalyzed by the enzyme orotidylate decarboxylase. Uncatalyzed, the decarboxylation reaction is extremely slow (estimated to occur on average one time per 78 million years). Adequately catalyzed, the reaction takes place once per second, an increase of 10¹⁷-fold.

In humans, the orotidylate decarboxylase function is carried out by the protein UMP synthase. Defective UMP synthase can result in orotic aciduria, a metabolic disorder.

Effects on animal intelligence

In a study, gerbils fed a combination of uridine monophosphate, choline, and docosahexaenoic acid (DHA) were found to have significantly improved performance in running mazes over those not fed the supplements, implying an increase in cognitive function.

In foods

In brain research studies, uridine monophosphate is used as a convenient delivery compound for uridine. Uridine is the active component of this compound. Uridine is present in many foods, mainly in the form of RNA. Non-phosphorylated uridine is not bioavailable beyond first-pass metabolism, as it is almost entirely catabolised in the liver and gastrointestinal tract.

See also

• Nucleoside
• Nucleotide
• DNA
• RNA
• Oligonucleotide
• Pyrimidine biosynthesis

UpToDate Contents

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English Journal

• Physiological characterization of a pyrimidine auxotroph exposes link between uracil phosphoribosyltransferase regulation and riboflavin production in Ashbya gossypii.

• Silva R, Aguiar TQ, Oliveira C, Domingues L.
• New biotechnology. 2019 May;50()1-8.
• The blockage of the de novo pyrimidine biosynthetic pathway at the orotidine-5'-phosphate decarboxylase level was previously demonstrated to affect riboflavin production in the industrial producer fungus Ashbya gossypii. However, the molecular basis for the unusual sensitivity to uracil displayed by
• PMID 30590201

• Preparation of titanium ion functionalized polydopamine coated ferroferric oxide core-shell magnetic particles for selective extraction of nucleotides from Cordyceps and Lentinus edodes.

• Zhou DD, Zhang H, Zhang Q, Qian ZM, Li WJ, Li CH, Yang FQ, Chen H.
• Journal of chromatography. A. 2019 Apr;1591()24-32.
• In this study, a titanium ion (Ti) functionalized polydopamine coated ferroferric oxide (FeO@PDA@Ti) core-shell magnetic particle was prepared for the selective extraction of nucleotides. Firstly, different metal ions including Ti, Zr, Fe, Al, Cu, Zn, Ni and Mg were respectively immobilized onto FeO
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Japanese Journal

• Effects of long-term cadmium exposure on urinary metabolite profiles in mice

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• … However, there are also some nucleotides (guanosine, guanosine monophosphate, cyclic AMP, uridine), amino acid derivatives (homoserine, <i>N</i>-acetyl-<i>L</i>-aspartate, <i>N</i>-acetylglutamine, acetyl-phenylalanine, carboxymethyllysine), and peptides. …
• NAID 130006404220

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• <b>Orotate phosphoribosyltransferase localizes to the Golgi complex and its expression levels affect the sensitivity to anti-cancer drug 5-fluor</b><b>ouracil </b>

• HOZUMI Yasukazu,TANAKA Toshiaki,NAKANO Tomoyuki,MATSUI Hirooki,NASU Takashi,KOIKE Shuji,KAKEHATA Seiji,ITO Tsukasa,GOTO Kaoru
• Biomedical Research 36(6), 403-409, 2015
• … It catalyzes oronitine to uridine monophosphate (UMP), which is used for RNA synthesis. …
• NAID 130005116835

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★リンクテーブル★

リンク元	「ウリジン一リン酸」「UMP」「uridylic acid」「UMP hydrolase 1 deficiency」「UMP synthase type 1 deficiency」
拡張検索	「deoxyuridine monophosphate」
関連記事	「monophosphate」

「ウリジン一リン酸」

　　[★]

英

uridine monophosphate、UMP

関

ウリジル酸

-UMP

同

uridine monophosphate

「UMP」

　　[★]

同

uridine monophosphate

同

uridine monophosphate

同

uridine monophosphate

「uridylic acid」

　　[★]

• ウリジル酸

関

UMP、uridine monophosphate

「UMP hydrolase 1 deficiency」

　　[★]

同

uridine monophosphate

「UMP synthase type 1 deficiency」

　　[★]

同

uridine monophosphate

「deoxyuridine monophosphate」

　　[★]

デオキシウリジン一リン酸

関

dUMP

「monophosphate」

　　[★]

• n.

• 一リン酸塩、一リン酸エステル、一リン酸